JP2020505395A5 - - Google Patents
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- Publication number
- JP2020505395A5 JP2020505395A5 JP2019540035A JP2019540035A JP2020505395A5 JP 2020505395 A5 JP2020505395 A5 JP 2020505395A5 JP 2019540035 A JP2019540035 A JP 2019540035A JP 2019540035 A JP2019540035 A JP 2019540035A JP 2020505395 A5 JP2020505395 A5 JP 2020505395A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- prodrug
- pharmaceutically acceptable
- acceptable salt
- stereoisomer
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- 150000001875 compounds Chemical class 0.000 claims description 67
- 125000000217 alkyl group Chemical group 0.000 claims description 36
- 239000000651 prodrug Substances 0.000 claims description 34
- 229940002612 prodrugs Drugs 0.000 claims description 34
- 150000003839 salts Chemical class 0.000 claims description 34
- 239000011780 sodium chloride Substances 0.000 claims description 34
- 102200124918 NRAS G12C Human genes 0.000 claims description 20
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 18
- 239000008194 pharmaceutical composition Substances 0.000 claims description 17
- 125000005843 halogen group Chemical group 0.000 claims description 16
- 102100009283 HRAS Human genes 0.000 claims description 14
- 101710033925 HRAS Proteins 0.000 claims description 14
- 102100009279 KRAS Human genes 0.000 claims description 14
- 101710033922 KRAS Proteins 0.000 claims description 14
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 14
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 14
- 125000001188 haloalkyl group Chemical group 0.000 claims description 14
- 125000001072 heteroaryl group Chemical group 0.000 claims description 14
- 125000000623 heterocyclic group Chemical group 0.000 claims description 14
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 201000011510 cancer Diseases 0.000 claims description 11
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 10
- 125000002837 carbocyclic group Chemical group 0.000 claims description 10
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 10
- 230000035772 mutation Effects 0.000 claims description 10
- 125000000304 alkynyl group Chemical group 0.000 claims description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- -1 heterocyclylene Chemical group 0.000 claims description 9
- 102200006538 KRAS G12C Human genes 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 102200006614 HRAS G12C Human genes 0.000 claims description 6
- 230000001404 mediated Effects 0.000 claims description 6
- 201000010099 disease Diseases 0.000 claims description 5
- 230000002401 inhibitory effect Effects 0.000 claims description 5
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 4
- 102000008300 Mutant Proteins Human genes 0.000 claims description 4
- 108010021466 Mutant Proteins Proteins 0.000 claims description 4
- 208000008443 Pancreatic Carcinoma Diseases 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 201000011231 colorectal cancer Diseases 0.000 claims description 4
- 201000005787 hematologic cancer Diseases 0.000 claims description 4
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 4
- 201000005202 lung cancer Diseases 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000004043 oxo group Chemical group O=* 0.000 claims description 4
- 201000002528 pancreatic cancer Diseases 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 235000018102 proteins Nutrition 0.000 claims description 4
- 102000004169 proteins and genes Human genes 0.000 claims description 4
- 108090000623 proteins and genes Proteins 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 206010027476 Metastasis Diseases 0.000 claims description 3
- 206010028980 Neoplasm Diseases 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N Amino radical Chemical group [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 2
- JYZIHLWOWKMNNX-UHFFFAOYSA-N Benzimidazole Chemical compound C1=C[CH]C2=NC=NC2=C1 JYZIHLWOWKMNNX-UHFFFAOYSA-N 0.000 claims description 2
- ZADPBFCGQRWHPN-UHFFFAOYSA-N OBO Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K [O-]P([O-])([O-])=O Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 2
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 2
- 125000005418 aryl aryl group Chemical group 0.000 claims description 2
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 claims description 2
- 125000000151 cysteine group Chemical group N[C@@H](CS)C(=O)* 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 230000000694 effects Effects 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 125000004474 heteroalkylene group Chemical group 0.000 claims description 2
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 2
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 2
- 125000001041 indolyl group Chemical group 0.000 claims description 2
- 238000002347 injection Methods 0.000 claims description 2
- 239000007924 injection Substances 0.000 claims description 2
- 125000005647 linker group Chemical group 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 239000010452 phosphate Substances 0.000 claims description 2
- 230000035755 proliferation Effects 0.000 claims description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 2
- 230000000155 isotopic Effects 0.000 claims 14
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 2
- 206010056981 Adenomatous polyposis coli Diseases 0.000 claims 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 150000002830 nitrogen compounds Chemical class 0.000 claims 1
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- BDYKZMNDOYRQTR-UHFFFAOYSA-N CC(C)(C)c(c(F)ccc1)c1O Chemical compound CC(C)(C)c(c(F)ccc1)c1O BDYKZMNDOYRQTR-UHFFFAOYSA-N 0.000 description 3
- BQBGTRIOPZRLJD-UHFFFAOYSA-N CC(C)(C)c1cc(O)cc2c1cccc2 Chemical compound CC(C)(C)c1cc(O)cc2c1cccc2 BQBGTRIOPZRLJD-UHFFFAOYSA-N 0.000 description 3
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2023
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